How To Founder

What if the price you're charging is teaching your customers your product isn't worth that much?

Most founders treat pricing as a math problem: add up costs, slap on a margin, done. But pricing expert Dan Balcauski reveals why this approach leaves massive value on the table. In this episode, we explore why your price is actually a positioning decision that determines everything from your sales motion to your customer quality...

You built something from nothing and somewhere along the way, you became "the person who does this." Your identity fused with your company, your role, your expertise. That merger felt like commitment. It was a trap.

The sunk cost dilemma runs deeper than money or time. It's about who you've become and the terrifying question of who you'd be without it. Founders hold onto failing strategies, dead partnerships, a...

You've known for months who needs to go. The documentation feels thin. The conversation you keep rehearsing never sounds right.

In this episode, staffing CEO Bill Kasko, who built Frontline Source Group to 31 locations over 25 years, breaks down why most termination problems are actually hiring problems. He shares the single interview question that reveals more about a candidate than nine rounds of interviews, explains why firin...

You handed it off. They dropped it. But what if the problem wasn't their execution?

In this episode, Chaz Wolfe, founder of Gathering the Kings Masterminds, breaks down the difference between delegation and abdication. He's built and sold multiple seven-figure companies and interviewed over 400 entrepreneurs, and his take on why most founders fail at delegation hits different. The issue isn't finding reliable people. It&...

Why do the least qualified candidates keep getting hired at the best startups?

Wistia's founders learned their best hires weren't credentialed specialists. They were self-starters who had built something on their own without anyone asking. In this episode we break down what startup founders are really evaluating when they hire, and it's not what job boards train you for. We cover what you're actually signing up for w...

What if the secret to raising capital isn't learning complex financial models, but building the same daily discipline that kept a restaurant owner alive on two weeks of cash reserves?

In this episode, we sit down with Heidi Knoblauch, who built Plum Oyster Bar, managed $180 million in venture funds, and now helps founders develop the financial instincts they need to succeed. Discover why most founders maintain three different se...

Your most profitable month might be your most dangerous. 

In 2015, Crumbs Bake Shop reported record revenue while filing for bankruptcy. Thirty locations. Profitable on paper. Couldn't make the next lease payment. The P&L lied. The bank account didn't.

In this episode, serial entrepreneur Colin Sanburg reveals the four "cash monsters" that devour businesses while founders celebrate paper profits. He breaks down ...

What do you owe someone in the thirty seconds after you've just ended their career?

Most founders prepare the spreadsheet, rehearse the legal script, and completely miss what actually matters: sitting across from someone whose identity is tied to a job that no longer exists. In this episode, Anthony, Chris, and Stephanie share their personal experiences on both sides of layoffs, the mistakes that make a hard conversation cruel, ...

What if your "growth" is actually a liability in an audit?

In this eye-opening episode, we sit down with former eBay and Sonos CFO Aman Verjee to demystify the brutal reality of going public. Most founders treat an IPO as an exit, but Aman reveals why it’s actually the start of a punishing new journey requiring a complete architectural overhaul. Discover the "invisible infrastructure" public companies possess tha...

What if the candidate with the perfect resume is actually your worst option?

Most founders default to experience when hiring. It feels safe. But that ten-year veteran from a Fortune 500 company has been trained to operate inside systems you don't have—and may never build. They expect structure, support, and clear swim lanes. Your startup offers chaos, ambiguity, and problems that don't fit job descriptions.

In this episode, w...

What if your org chart is actually lying to you?

Those neat boxes and reporting lines suggest work flows predictably from one function to the next. But watch what happens when a customer complaint lands. It bounces between departments while everyone optimizes for their own metrics. The customer waits. The system fails.

In this episode, we sit down with Todd Hagopian, author of The Unfair Advantage, to explore why treating your organi...

Your marketing team hit their numbers. Your sales team says the leads are trash. Both are right, and that's the structural failure you built.

In this episode, Jon Ferrara, founder of Goldmine and Nimble, reveals why the marketing-sales war isn't a people problem. It's a compensation problem. Marketing gets bonused on MQLs. Sales gets bonused on closed deals. The gap between those metrics is a war zone you funded.

Jon spen...

You've known for months. The employee who was great in year one but can't grow with the company. The customer who's been with you since the beginning but costs more to serve than they pay. The prices you set when you were desperate that no longer make sense.You know what you should do. But knowing isn't the hard part.The hard part is that you actually care about these people. You remember when they believed in you b...

What if the skills that made you successful are now holding your company back?

Rand Fishkin built Moz to 150 employees before admitting he'd become the company's biggest bottleneck. His mistake wasn't incompetence. He kept doing the job that worked at fifteen people.

In this episode, we map the specific shifts required at each growth milestone. What behaviors to abandon. What new muscles to build. Why the ceiling you'...

Your pipeline is lying to you.

A sales coach tracked a client's team for ninety days and found forty percent of their pipeline would never close. Those zombie deals weren't just dead weight. They were stealing attention from the fifteen percent that could actually convert.

Most founders treat every lead like a lottery ticket, terrified that the one they disqualify might have been the big win. So they chase. They follow up. Th...

You're staring at the decision: hire your first person or stay solo. Everyone says you need a team to scale. But what if they're wrong?

Jason Cohen ran SmartBear Software solo at seven figures and turned down acquisitions because staying solo was his competitive advantage. This episode isn't about choosing the "right" path—it's about understanding you're choosing between two different games. Solo gives ...

What if your alignment meetings are just expensive procrastination?

Jared Christopher built Yellowfin BI's sales team to 340% revenue growth in two years without a single alignment meeting. Each regional director had complete authority with one rule: defend your decisions with data. While competitors held stakeholder sessions, Yellowfin shipped.

In this episode, Blima Ehrentreu, founder and CEO of The Designers Group, breaks down...

What if paying people to show up is the problem?

Joey Rockey has built 29 businesses, with 25 now running without him. His secret isn't better delegation or time management. It's designing businesses where employees get paid for results, not hours. Hotel housekeepers who finish by noon and earn more than hourly workers. Marketing teams compensated per customer acquired who iterate in real time. Line cooks paid on attendance ...

Most founders think organizational design is something you do once you're big. Wrong.

Your company already has structure. Communication patterns exist. Informal networks formed the day your second employee started. The only question is whether you designed it or it designed itself. Chris and Stephanie break down when structure helps versus when it kills momentum. They explore why startups fail by copying big company org charts, ...